This invention relates to the preparation of (2-(6-substituted)pyridinyloxy)alkanols from 2-(6-substituted)pyridinols and organic carbonates.
Newkome et al., "Chemistry of Heterocyclic Compounds. 23. Synthesis of Multiheteromacrocycles Posessing 2,6-Pyridino Subunits Connected by Carbon Oxygen Linkages", J. Org. Chem., 42(9), 1500 (1977), teach that 2-(2-pyridinyloxy)ethanol can be prepared by reacting a 2-bromopyridine with a dianion of ethylene glycol, which was generated from sodium hydride and ethylene glycol.
Yoshino et al., "Synthetic Studies with Carbonates", J. C. S. Perkins I, 1266 (1977), teach that the reaction of a 2-pyridinol with an ethylene carbonate affords only 1-(2-hydroxyethyl)-2-pyridone. Yields of up to 75 percent of the 1-(2-hydroxyethyl)-2-pyridone are reported.
A novel process for preparing (2-(6-substituted)pyridinyloxy)alkanols in high yields has been discovered.